Boron trichloride/tetra-n-butylammonium iodide: A mild, selective combination reagent for the cleavage of primary alkyl aryl ethers

…, MG Vetelino, DM Rescek, GF Woodworth…

Index: Brooks, Paige R.; Wirtz, Michael C.; Vetelino, Michael G.; Rescek, Diane M.; Woodworth, Graeme F.; Morgan, Bradley P.; Coe, Jotham W. Journal of Organic Chemistry, 1999 , vol. 64, # 26 p. 9719 - 9721

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Citation Number: 101

Abstract

A number of reagents are routinely used to cleave primary alkyl aryl ethers1 such as BBr3, 2 EtSNa/DMF, 3 TMSI, 4 py-HCl, 5 and HBr/AcOH. 6, 7 Boron-based reagents are particularly versatile for this transformation, as the Lewis acidity of the boron center and the nucleophilic nature of the ligands can be effectively manipulated (eg, 2-bromo-1, 3, 2-benzodioxaborole, 8 9-Br-BBN, 9and Me2-BBr10). We report herein that a mixture of BCl3 and anhydrous n- ...